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WO2009134382A3 - Cyclopeptides containing rgd mimetics as imaging markers for integrins - Google Patents

Cyclopeptides containing rgd mimetics as imaging markers for integrins Download PDF

Info

Publication number
WO2009134382A3
WO2009134382A3 PCT/US2009/002627 US2009002627W WO2009134382A3 WO 2009134382 A3 WO2009134382 A3 WO 2009134382A3 US 2009002627 W US2009002627 W US 2009002627W WO 2009134382 A3 WO2009134382 A3 WO 2009134382A3
Authority
WO
WIPO (PCT)
Prior art keywords
integrins
polypeptides
imaging markers
containing rgd
rgd mimetics
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2009/002627
Other languages
French (fr)
Other versions
WO2009134382A2 (en
Inventor
Hartmuth C. Kolb
Kai Chen
Joseph C. Walsh
Qianwa Liang
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Siemens Medical Solutions USA Inc
Original Assignee
Siemens Medical Solutions USA Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Siemens Medical Solutions USA Inc filed Critical Siemens Medical Solutions USA Inc
Publication of WO2009134382A2 publication Critical patent/WO2009134382A2/en
Publication of WO2009134382A3 publication Critical patent/WO2009134382A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/64—Cyclic peptides containing only normal peptide links
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
    • A61K51/04—Organic compounds
    • A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
    • A61K51/082—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins the peptide being a RGD-containing peptide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
    • A61K51/04—Organic compounds
    • A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
    • A61K51/088—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins conjugates with carriers being peptides, polyamino acids or proteins
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N2333/00—Assays involving biological materials from specific organisms or of a specific nature
    • G01N2333/435—Assays involving biological materials from specific organisms or of a specific nature from animals; from humans
    • G01N2333/705—Assays involving receptors, cell surface antigens or cell surface determinants
    • G01N2333/70546—Integrin superfamily, e.g. VLAs, leuCAM, GPIIb/GPIIIa, LPAM

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

Abstract

Radiolabeled cyclic polypeptides, pharmaceutical compositions comprising radiolabeled cyclic polypeptides, and methods of using the radiolabeled cyclic polypeptides. Such polypeptides can be used in imaging studies, such as Positron Emitting Tomography (PET) or Single Photon Emission Computed Tomography (SPECT). The radionuclide label is a positron or gamma emitter, e.g. 18F. The polypeptide core is a backbone cyclic RGD derivative of formula: (I) wherein R1 and R8 are side chains of natural or unnatural amino acids and w is an integer from 1 to 5.
PCT/US2009/002627 2008-04-30 2009-04-30 Cyclopeptides containing rgd mimetics as imaging markers for integrins Ceased WO2009134382A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US4938508P 2008-04-30 2008-04-30
US61/049,385 2008-04-30

Publications (2)

Publication Number Publication Date
WO2009134382A2 WO2009134382A2 (en) 2009-11-05
WO2009134382A3 true WO2009134382A3 (en) 2009-12-30

Family

ID=40872298

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2009/002627 Ceased WO2009134382A2 (en) 2008-04-30 2009-04-30 Cyclopeptides containing rgd mimetics as imaging markers for integrins

Country Status (2)

Country Link
US (1) US8133472B2 (en)
WO (1) WO2009134382A2 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009018175A2 (en) * 2007-07-27 2009-02-05 Siemens Medical Solutions Usa, Inc. Cyclic azapeptides as integrin markers
US8263133B2 (en) * 2009-02-18 2012-09-11 The Regents Of The University Of California Multivalent clustering targeting strategy for drug carriers
EP2380596A1 (en) 2010-04-20 2011-10-26 Technische Universität München Cyclopentapeptide derivatives and uses thereof
US9234007B2 (en) 2012-07-02 2016-01-12 University Of South Florida RGD mimetic γ-AApeptides and methods of use
WO2014197500A1 (en) * 2013-06-03 2014-12-11 University Of Southern California Targeted crosslinked multilamellar liposomes
WO2015031084A1 (en) 2013-08-28 2015-03-05 Jianfeng Cai Methods of synthesizing y-aapeptides, y-aapeptide building blocks, y-aapeptide libraries, and y-aapeptide inhibitors of ab40 aggregates
AU2014396468B2 (en) 2014-06-06 2019-02-21 Technische Universitat Munchen Modified cyclopentapeptides and uses thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008033561A2 (en) * 2006-09-15 2008-03-20 Siemens Medical Solutions Usa, Inc. Click chemistry-derived cyclopeptide derivatives as imaging agents for integrins

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19728524A1 (en) 1997-07-04 1999-01-07 Merck Patent Gmbh Cyclic azapeptides
US6537520B1 (en) * 1998-03-31 2003-03-25 Bristol-Myers Squibb Pharma Company Pharmaceuticals for the imaging of angiogenic disorders
US20030125243A1 (en) * 2000-07-20 2003-07-03 Jun Liu Synthesis of cyclic peptides
EP1733742A1 (en) 2005-06-17 2006-12-20 Universiteit Utrecht Holding B.V. Dendrimers multivalently substituted with active groups
AU2006277117B2 (en) 2005-08-05 2013-01-10 Syntarga B.V. Triazole-containing releasable linkers and conjugates comprising the same
US20080213175A1 (en) 2006-09-15 2008-09-04 Kolb Hartmuth C Click chemistry-derived cyclic peptidomimetics as integrin markers
WO2009018175A2 (en) * 2007-07-27 2009-02-05 Siemens Medical Solutions Usa, Inc. Cyclic azapeptides as integrin markers

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008033561A2 (en) * 2006-09-15 2008-03-20 Siemens Medical Solutions Usa, Inc. Click chemistry-derived cyclopeptide derivatives as imaging agents for integrins

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
CHEN XIAOYUAN ET AL: "Pegylated Arg-Gly-Asp peptide:64 Cu labeling and PET imaging of brain tumor alphavbeta3-integrin expression", JOURNAL OF NUCLEAR MEDICINE, vol. 45, no. 10, October 2004 (2004-10-01), pages 1776 - 1783, XP002538420, ISSN: 0161-5505 *
DIJKGRAAF INGRID ET AL: "Synthesis of DOTA-conjugated multivalent cyclic-RGD peptide dendrimers via 1,3-dipolar cycloaddition and their biological evaluation: implications for tumor targeting and tumor imaging purposes", ORGANIC AND BIOMOLECULAR CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, CAMBRIDGE, GB, vol. 5, no. 6, 21 March 2007 (2007-03-21), pages 935 - 944, XP002470091, ISSN: 1477-0520 *
HAMIDPOUR MOHSEN ET AL: "The isolation and characterisation of antiplatelet antibodies", EUROPEAN JOURNAL OF HAEMATOLOGY, vol. 76, no. 4, April 2006 (2006-04-01), pages 331 - 338, XP002538413, ISSN: 0902-4441 *
JEONG JAE MIN ET AL: "Preparation of a promising angiogenesis PET imaging agent: Ga-68-labeled c(RGDyK)-isothiocyanatobenzyl-1,4,7-triazacyclononane-1 ,4,7-triacetic acid and feasibility studies in mice", JOURNAL OF NUCLEAR MEDICINE, vol. 49, no. 5, May 2008 (2008-05-01), pages 830 - 836, XP002538417, ISSN: 0161-5505 *
LI ZI-BO ET AL: "Click chemistry for (18)F-labeling of RGD peptides and microPET imaging of tumor integrin alphavbeta3 expression", BIOCONJUGATE CHEMISTRY, ACS, WASHINGTON, DC, US, vol. 18, no. 6, 1 November 2007 (2007-11-01), pages 1987 - 1994, XP002470093, ISSN: 1043-1802 *
RYPPA CLAUDIA ET AL: "In vitro and in vivo evaluation of doxorubicin conjugates with the divalent peptide E-[c(RGDfK)(2)] that targets integrin alpha(v)beta(3)", BIOCONJUGATE CHEMISTRY, vol. 19, no. 7, July 2008 (2008-07-01), pages 1414 - 1422, XP002538414, ISSN: 1043-1802 *

Also Published As

Publication number Publication date
US20100074844A1 (en) 2010-03-25
US8133472B2 (en) 2012-03-13
WO2009134382A2 (en) 2009-11-05

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